The Question I Ask Every New Executive

April 23, 2026

I’ve interviewed thousands of executives. I ask them all the same opening question: “Tell me about a time you were wrong.”

Why it works

The answer tells you three things. First, whether they’re self-aware enough to know they’ve been wrong — many aren’t. Second, whether they can discuss failure without blame or spin. Third, whether they actually learned anything or just got unlucky.

The red flags

“I can’t think of one” is disqualifying. So is any answer that starts with “I was wrong, but…” The “but” is the tell. Real self-awareness doesn’t need a defense attorney.

The green flags

The best answers are specific, unflattering, and end with a lesson the candidate still applies today. “I hired the wrong VP of Sales in 2019. Here’s what I missed. Here’s what I do differently now.” That’s an executive who’s going to make your company better.

The deeper point

Every executive has been wrong — many times. The ones who’ve processed it become great leaders. The ones who haven’t become liabilities at scale. The question is how much damage they do before you find out.

Want Bill to speak to your team, board, or event?

Bill Canady keynotes sharpen middle market executives on turnaround, profitable growth, and the 80/20 discipline behind $3B+ in enterprise value. Inquire about speaking engagements at billcanady.com.

About the Author

Bill Canady

Bill Canady is a national best-selling author, Founder & CEO of The 80/20 Institute, and a global business leader known for transforming companies into high-performing, profitable enterprises. Over the course of his career, Bill has led multibillion-dollar organizations through their most critical challenges—navigating complex regulatory, investor, and media environments—while consistently delivering profitable growth.

Drawing on decades of executive experience, Bill created the Profitable Growth Operating System (PGOS), a proven framework designed to help leaders cut complexity, focus on the critical few, and accelerate growth. Through The 80/20 Institute, he and his team partner with CEOs, executives, and entrepreneurs worldwide to apply the 80/20 methodology in real-world settings, unlocking revenue growth, margin expansion, and shareholder value.

As both an operator and advisor, Bill’s mission is clear: to give leaders the tools, systems, and confidence they need to achieve sustainable, profitable growth — without sacrificing focus, culture, or execution.

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